2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-ol hydrochloride

• ChemBase ID: 72582
• Molecular Formular: C28H28ClNO4S
• Molecular Mass: 510.04422
• Monoisotopic Mass: 509.14275706
• SMILES: c1(ccc2c(c1)sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O)O.Cl
• Canonical SMILES: Oc1ccc2c(c1)sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O.Cl
• InChI: InChI=1S/C28H27NO4S.ClH/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29;/h4-13,18,30-31H,1-3,14-17H2;1H
• InChIKey: BKXVVCILCIUCLG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-ol hydrochloride
• IUPAC Traditional name: raloxifene hydrochloride; 2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-ol hydrochloride
• Synonyms: Keoxifene hydrochloride; LY 156758; [6-Hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride; Raloxifene hydrochloride; [6-Hydroxy-2-(4-hydroxyphenyl)-benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone Hydrochloride; LY-139481; Evista; Raloxifene Hydrochloride; (6-Hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone hydrochloride; Raloxifene Hydrochloride; keoxifene; Evista(Raloxifene Hydrochloride; 2-(4-hydroxyphenyl)-3-({4-[2-(piperidin-1-yl)ethoxy]phenyl}carbonyl)-1-benzothiophen-6-ol hydrochloride

Database IDs

• CAS Number: 82640-04-8
• MDL Number: MFCD01938233
• PubChem SID: 162037507; 24278673
• PubChem CID: 54900

CALCULATED PROPERTIES

• Acid pKa: 8.892227
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.586806
• LogD (pH = 7.4): 5.3366327
• Log P: 5.6926293
• Molar Refractivity: 135.48 cm^3
• Polarizability: 54.715824 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble28 mg/mL; H2O: insoluble; Methanol
• Apperance: light yellow solid; Light-Yellow Solid
• Melting Point: 250-253°C; 266 - 268°C
• Hydrophobicity(logP): 6.861

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: estrogen receptor

Product Information

• Purity: 95%; 95+%
• Salt Data: Hydrochloride
• Empirical Formula (Hill Notation): C28H27NO4S · HCl

DETAILS

Selleck Chemicals - S1227

Research Area: Cancer
Biological Activity:
Raloxifene has estrogen and tamoxifen-like effects on bone and serum cholesterol levels in ovariectomized rats. At 5 weeks, ovariectomy induced a 9% and 18% decrease in the bone mineral density of the lumbar vertebrae L1-4 and proximal tibiae, respectively. Raloxifene prevented this loss of bone with EC50=0.3 mg/kg/day for both the axial and appendicular skeleton. [1]Raloxifene, which demonstrated an extremely low IC50 value of 2.9 nM for phthalazine oxidase in human liver cytosol. [2]References on Evista(Raloxifene HCl)[] DMD, 2004, 32:89–97

Sigma Aldrich - R1402

Biochem/physiol Actions
Raloxifene is a selective estrogen receptor modulator (SERM); acts as an anti-estrogen in both breast and uterine tissue while being estrogenic in bone. May have efficacy against estrogen-sensitive cancers.

Toronto Research Chemicals - R100000

A nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic.Insoluble in water.

REFERENCES

• Masahiko Sato et al. J Bone Miner Met. 1994
• Jone, C.D., et al.: J. Med. Chem., 27, 1057 (1984)
• Buelke-Sam, J., et al.: Reprod. Toxicol., 12, 217 (1984)